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DOI: 10.1055/sos-SD-207-00308

Chartoire, A.; Nolan, S. P.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (20131523.

Acylsilanes 39 can be coupled with various organic halides in the presence of copper, and in some cases palladium, to yield the corresponding enol silyl ethers 40/41 (Scheme 10).[‌39‌] The first step involves the generation of an alkenylcopper species by 1,2-C(sp2)-to-O silyl migration of the acylsilane using tert-butoxycopper(I) in dimethylformamide. The cross coupling is then achieved by adding a halide. If the halide is allylic, benzylic, or an alkyl derivative, the reaction does not require palladium to form products 40. On the other hand, if the halide is an aryl or a vinyl derivative, then the reaction requires the use of a catalytic amount of tetrakis(triphenylphosphine)palladium(0) for the formation of products 41.

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